3‐(α,α‐DIMETHYLALLYL)‐PSORALEN: A LINEAR FUROCOUMARIN FORMING MAINLY 4‘,5’‐MONOFUNCTIONAL ADDUCTS WITH DNA

Publisher Website
Google Scholar
Abstract
Abstract— 3‐(α,αdimethylallyl)‐psoralen, a furocoumarin derivative recently isolated from Hortia arborea. has been studied with regard to its photoreacting (365 nm) capacity with native DNA. This compound photobinds to DNA to a much lower extent than psoralen, forming mainly 4.5′‐monofunc‐tional adducts, due to the presence in the 3‐position of α.α‐dimethylallyl group. which exerts a considerable hindrance both for the formation of a molecular complex with native DNA and for the photoreaction of the3,4‐double bond. This site of the molecule photoreacts, and, only 2.5% of the bound substance forms cross‐linkages. Therefore. 3‐(α,α‐dimethylallyl).psoralen behaves as a fairly pure mono‐functional reagent.